


High on Sinning

by thewinchesterlifestyle



Category: Supernatural
Genre: Age Difference, Alternate Universe, Alternate Universe - College/University, Barebacking, Bondage, Bottom Dean, Bottom Sam Winchester, Butt Plugs, Cock Rings, Dirty Talk, Drugs, Gags, M/M, Manipulation, Mildly Dubious Consent, Morally Ambiguous Character, Naive Sam Winchester, Name-Calling, Older Castiel, Open Relationships, Orgasm Delay/Denial, References to internalized Homophobia, Religious Dean Winchester, Rough Sex, Semi-Public Sex, Size Difference, Slut Castiel, Spanking, Stoner Castiel, Teen Dean Winchester, Teen Sam Winchester, Top Castiel, Underage - Freeform, at the beginning because of the way the winchesters were raised
Language: English
Status: Completed
Published: 2018-02-19
Updated: 2018-02-19
Packaged: 2019-03-21 01:02:51
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 6,061
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13729815
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: “It’s a sin, Cas.” he hissed out when Castiel’s long fingers stroked over the front of his pants and Castiel leaned in with a suggestive grin. “If you went to church you might learn something.” Dean’s eyes narrowed when Castiel seemed to brush his comment off.





	1. Chapter 1

**Author's Note:**

> This was written for a series of prompts. Split into chapters instead of simply using page breaks due to there being undefined time skips.
> 
> FYI: If you want to skip the Cas/Sam, since I know that isn't for everyone, just stop reading after chapter 3 because that's all chapter 4 is.

Castiel had noticed the pretty green eyes first and quickly noticed the guy’s lips second. Both were set on a pretty face and below that a delightful body. It had only taken a little observation as he relaxed against a tree to realize that he was very interested in seducing the pretty college student. It was even more evident when he’d caught sight of a _very_ plump looking ass he was more than interested in fucking.

The first attempt at seducing Dean Winchester ended poorly when Dean freaked out at his advances but it hadn’t stopped Castiel from continuing to seek him out. Castiel made a habit of bumping into him at the coffee shop, in class, on campus and at campus events. Each time Dean resisted a little less and Castiel’s relaxed seduction started to work.

Fucking random pretty co-eds on campus and hook-ups at bars helped pass the time when he wasn’t trying actively to get into Dean’s pants.

Dean’s skittish behavior didn’t deter him. Castiel had  _always_  been able to get whoever he set his sights on; his long list of hook-ups was a testament to that fact. It didn’t matter that this particular interest was taking longer when there were plenty of willing people to fuck otherwise. Castiel never wanted for partners, a pretty high school boy who moaned like a whore like taking his cock or the vivacious red head who vigorously rode his cock like she was paid to do it, as he sought to win Dean over.

Castiel grinned lazily as he looked over at Dean with glassy eyes and a relaxed smile that had Dean shifting uncomfortably. “It’s a sin, Cas.” he hissed out when Castiel’s long fingers stroked over the front of his pants and Castiel leaned in with a suggestive grin. “If you went to church you might learn something.” Dean’s eyes narrowed when Castiel seemed to brush his comment off.

Dean had thought if he stopped reacting Castiel would stop his advances but the stoner who always seemed to be on campus had only gotten bolder. It wasn’t like Dean hadn’t noticed the attention Castiel always received. Guys and girls alike practically flocked to him with interest lighting their faces and obvious in every line of their bodies.

“I know something I’d rather learn more.” the lazy smile had Dean’s eyebrow raising as he shifted slightly and shied away from the pleasure of Castiel rubbing against the front of his pants. “I would love to learn how many times I would have to spank you until that first tear falls and how long you can be denied orgasm before you’re begging me to fuck you within an inch of your life.” he leaned closer, “I’d rather learn what it feels like to slowly open that virgin hole of yours up and stuff it full with my dick. I want to learn how it feels to have your ass clenching around me as I fuck you into the mattress until you can’t move and you walk with a limp for days.”

Dean’s cheeks were flushed darkly and his eyes widened as Castiel smiled slowly at him.

“There are many things I would rather learn and most of them involve that fuckable ass of yours.”

Castiel’s hand never stopped rubbing until it was clear that he had felt Dean hardening. Dean jerked at the unexpected reaction. “Why don’t you find someone else?” even as he asked Dean didn’t shove Castiel’s hand away. Weeks of twitching at unexpected touches and shoving the stoner away had steadily changed into reluctant acceptance. The answer was always the same and Dean shifted away with a soft sound as he shook his head, “It’s a sin.”

It had been drilled into his head for  _years_. He’d known there would be temptation when he’d gone to college but Dean was barely into his first year and only eighteen years old.

A month later saw Dean bent over Castiel’s lap as Castiel viciously brought down a paddle on Dean’s reddening ass once more. “Seven.” he breathed when Dean gasped and clutched at air as his body jolted in pain. Another swat came down, “Eight.” Dean clenched his eyes closed. His cheeks were heated for multiple reasons and he prayed his parents never saw him like this.

He prayed that they never figured out he’d given into temptation and was letting another man touch him. That they never learned that he’d given in to letting another man inside his body whenever that other man wanted.

His ass had been fucked and used frequently after the first time he’d given in and Castiel frequently fucked his mouth whenever the need arose when he had Dean hit his knees.

“Uh.” the sound slipped out and Castiel stilled his spanking to regard the back of Dean’s head when he felt a slight tremor running through his  _boyfriend_ , the thought had an amused smile tugging at his lips at how misplaced it was, while he waited a beat. Having some kind of title for what they had, though it wasn’t exclusive in the least and Castiel frequently indulged in sex with a delicious variety of people, seemed to go a long way for Dean and Castiel indulged him. He’d let Dean call himself his boyfriend if it meant Dean was less resistant to letting Castiel fuck him as he pleased. “‘m fine.” the words were rough but Castiel pushed forward.

Castiel loved how Dean’s voice broken, flooded with tears, and how much better the sex seemed to be after he’d spanked Dean’s ass cherry red.

He continued to spank Dean’s ass until he heard the first hitch in Dean’s breathing and knew Dean was a step away from releasing a sob. “You did good.” he grinned lazily and stroked a hand over Dean’s heated flesh with satisfaction. It had taken quite a bit to get to this point where the very religious college freshman would let him anywhere near him. “I might take that cockring off after I’m done fucking you until you’re sobbing for more.” 

After Castiel rubbed lotion onto Dean’s warm skin Dean was shifted on his lap so he straddled Castiel. The thirty three year old dragged Dean in for a kiss as his fingers stroked down Dean’s shaking body.

Dean’s ass felt like it was on fire but the soft touches and warm kisses had him leaning in for more. His mind still tried to rebel at the thought of letting another man touch him but Castiel had to be different. This whole thing had to be different and that should make it fine.

“Cas.” he gasped it and flushed when arousal curled in his belly. Shame and humiliation had him squirming.

It was obvious that Castiel recognized the signs by now. He reached between them to stroke at Dean’s half-hard cock, teasing where the cockring rested, until Dean started to shake in his lap with little pleasured gasps escaping.

“You’re so pretty.” Castiel breathed out and sucked a mark into the skin of Dean’s neck. Castiel moved his mouth and bit lightly until a whimper escaped. “You’re even more pretty when you’re split open on my dick and I’m fucking you hard.” another whimper escaped and Castiel twisted his fingers at the head of Dean’s cock. “Did you prepare for me like I asked?” he dragged his tongue up the column of Dean’s neck before pressing a soft kiss behind Dean’s ear.

Castiel grabbed onto Dean and Dean moved with him until he was sprawled out on the sheets. His fingers gripped at Dean’s legs once he was ready and long fingers prodded at Dean’s entrance. Two sunk in easily and he grinned at the slick heat. Castiel was pleased that it seemed he’d trained Dean well. “Oh.” Dean’s mouth dropped open when they brushed against his prostate and stroked until Dean was spreading his legs wider as he clenched down.

For so many protests Dean turned out to be a pleasure-whore.

“You should always be a needy mess. Begging to be filled up. Need a good fucking each day don’t you, baby?” he smiled as Dean whined and twisted on the sheets as Castiel played his preppy little church boy like a fine instrument. Dean bowed beautifully and released such beautiful sounds that Castiel wished to record them. He loved listening to music and Dean moaning, begging for him, was beautiful music to him after so many refusals. “Do you want me to fuck you now? Push into that hot little body of yours and press you into the mattress? Fuck my dick into you until you can’t breathe?”

Dean nodded, too far gone to even care at this point, as fingers finally pulled out. Castiel worked on a condom, slicked himself up, before he guided the head of his cock towards Dean’s hole. He pushed in a few inches as Dean squirmed at the steady feeling of full.

Then fingers dug into Dean’s hips and Castiel buried himself to the hilt as Dean clenched down around him. He leaned forward to nip at Dean’s collarbone before moving back and starting up a punishing pace. Fucking forward quickly as he aimed for Dean’s prostate and watched how that pretty flush spread across Dean’s freckled cheeks. He’d had no problem slowly working towards having Dean under him.

He was easy going and fortunately for him that had put Dean at ease. But now he’d gotten the reluctant pretty guy who attended church each week, who knew all the words by heart and flushed with shame the first time that Castiel had dragged him into his lap to steal a kiss, and Castiel relished it. That same boy who told him it was a sin was moaning like a whore under him and clenching around him with a perfect tightness that he wanted to spend hours rewarding Dean for letting him fuck him.

Castiel slammed into Dean as his balls slapped against the green eyed college student with a delightfully lewd sound. “So tight for me. Such a tight hot little hole that’s always so greedy for my dick. I bet you could take my dick and a dildo together. You’d look so pretty stuffed even fuller.” the words were rough and Dean shoved his head back into the pillows as he started begging. Castiel couldn’t make out the words but the feeling was more than obvious. “Bet you’d look gorgeous getting fucked at both ends and used like a toy for a gangbang. Fucked full of come and begging for more dick.”

Dean’s small hard cock lay neglected and leaked precome as Dean’s legs locked around him. “ _Please_.” It was the one word Castiel could make out along with his name being chanted in an increasingly strung out voice. Dean tried to grab at him but Castiel pinned his hands down and kept thrusting until he finally came with a pleased moan.

“Could fuck you all day.”

“If you did that when would you get high?” Dean growled the words in frustration and Castiel grinned brightly at him. He was riding the high of his orgasm and he was pleased that repeatedly fucking Dean had him loosening up. Castiel pulled out and removed his condom before tossing it at his trash.

“I could fuck you and get high at the same time.” he reached over to stroke at Dean’s belly before moving down to remove the cockring. It took one light touch before Dean came all over himself. Dean’s moan was almost inhuman and Castiel grinned as Dean laid there panting. His muscles were lax as Castiel shifted and reached for a smoke. Dean didn’t bother moving as smoke started to fill the air and Castiel knew Dean could see the relaxed expression stealing over his features.

“That isn’t good for you.” Dean muttered but it only earned a laugh and fingers ruffling his hair with amusement. Dean watched Castiel stand up and move into the bathroom before returning with a washrag. He wiped Dean clean, tossed the rag towards his laundry basket, and then tossed a cover over Dean.

He glanced down at the freckled eighteen year old and then flicked his eyes towards Dean’s bag. “I might have to tie your hands behind your back next time.”

“With what?” it was sleepy and Castiel paused to stare at Dean who didn’t seem to realize what Castiel had actually said.

 “Your rosary.”


	2. Chapter 2

Castiel smiled politely at Dean’s parents as he answered each question he was asked. “Why didn’t you tell us you have such a sweet friend, Dean?” Mary questioned as she grinned at Castiel who offered another bright smile. “Honestly it is a relief to know you’ve made good friends at your university.”

She had no idea that Castiel was in his thirties and not a Graduate student like Castiel had insinuated. Or that Castiel was not part of his church. It was likely that Mary was just happy that he had found someone who seemed mature and knowledgeable who, she believed, would be a good influence on him.

Dean tensed slightly when he felt Castiel’s hand on his leg, felt it moving up, before he forced himself to relax. “I guess I was lucky.” he picked up his fork and brought another bite to his mouth all the while mentally struggling not to react.

When he shifted on his seat he could feel the thick dildo that Castiel had insisted he wear for the dinner, the one that he could see outlined under the thin skin of his belly, as Dean felt his cheeks heat up at the feeling. “I was worrying about you going to a different church but I’m sure you’ve got your friend there with you and Castiel will be able to help you adjust to campus.”

“Yes. I enjoy spending my Sunday’s with Dean.” Castiel moved his hand further up Dean’s leg and pressed against Dean’s slowly growing erection. “There is nothing like spending your Sunday sharing such important lessons.”

“That’s great!” Mary grinned again and bumped against her husband. If only she knew the lessons in question were how far Castiel could push Dean until he was begging for release or how many toys he could fit in Dean’s ass until his hole gaped.

“Yes.” Castiel agreed as he looked over to see Dean was done eating, “Do you need help collecting the dishes?”

“Oh that’s just…” Mary trailed off and Dean stared as his mother smiled again. “Thank you Castiel but Sam does the dinner dishes. And you’re our guest.” she placed her fork down, “Why don’t you two go upstairs and Dean can show you around, if you want.”

“That sounds great, Mrs. Winchester.” Castiel slowly moved back from the table and glanced at Dean before looking at Mary once more. “Thank you for the delicious meal.”

“You’re welcome. It’s just so nice that Dean found such a good influence involved in the church and on campus.” she watched as Castiel waited for her oldest son to get to his feet and then watched them leave them room. “He is such a sweet boy.”

“It’s good that Dean found a well-rounded friend. Hopefully he’ll be able to help guide Dean.” John agreed as Sam glanced at both of them with a slightly raised brow.

Upstairs Castiel followed Dean towards the younger male’s bedroom and the second they were inside he pressed him up against the door while locking it. “I’m going to fuck you up here.” he breathed out and nipped at Dean’s skin. “I’m going to fuck that greedy hole of yours while your family is downstairs and then keep my come in your ass with that toy you’re keeping warm for me.”

He tugged Dean away and looked at the bed before deciding on the carpet. Castiel knew he wouldn’t be able to control himself and a banging headboard would, unfortunately, give them away.

Castiel had Dean’s clothes off in record time and his own following quickly as he shifted Dean into a good position for fucking. He had that pretty ass up in the air, Dean’s legs spread and his cheek pressed against the carpet.

The monstrous dildo spread Dean’s round cheeks wide and had Castiel groaning.

“Fuck. Look at your hole around that dildo.” he pulled on it and fucked it hard into Dean as hitches of breath escaped. “Better be quiet,  _sweetheart_.” he bit lightly against Dean’s ass and felt the jolt at the feeling. “Do you need something to bite down on or can you keep your moans quiet?”

Instead Dean shoved his face against his arm while Castiel pulled the long dildo out and pressed his finger against Dean’s rim. “ _Please_.” it was hoarse and Castiel grinned wickedly.

He wasn’t high or even drunk, Castiel had wanted to be completely sober for today, but he didn’t need to be with the feelings this whole scene was giving him. It was a different kind of high and he ignored the fact that he couldn’t get high until they left as he positioned his cock at Dean’s entrance.

“Do try to keep those slutty moans to yourself unless you want your mother and father to know there is a man upstairs fucking their precious baby boy like the common little whore he has become.”

After those words Castiel thrust forward and groaned at the feeling of Dean’s warm hole wrapped around him. The pretty Freshman was still wet from earlier as Castiel drew back and snapped his hips forward.

He kept his hand braced on Dean, holding him in place, as he started up a hard and quick rhythm that had Dean’s breathing hitching as his cock filled. “There we go.” Castiel grinned as he felt Dean’s hole rhythmically flexing around him. “Your family is downstairs, Dean.” he breathed out and felt Dean’s ass tighten around him. “Right under us and you’re getting fucked by a man. There is a dick pumping inside that slutty hole of yours.” He nipped at Dean’s shoulder, “You’re taking it up the ass while your family is downstairs thinking you’re a good boy.”

“Oh oh I—” Dean bit his arm and clenched his eyes shut as Castiel changed his angle to get at Dean’s prostate. He kept up the pace, balls slapping loudly against Dean, until he reached around to start teasing Dean’s small cock.

“So hard for me. Love getting fucked, don’t you? Pretty little sinner.” he purred and felt Dean shaking under him as he shoved back into each thrust. “I’m so glad we could cross this off my list.” he draped over Dean and kept stroking him as his hips moved. The words escaping him were rough and Castiel punctuated them with pleasured sounds once in awhile as Dean shook under him. “Your church is on my list too.”

That comment earned a strangled sound and Castiel felt Dean’s cock jerking in his hold as the green eyed church boy came.

"That make you hot, Dean?” he grinned and thrust harder as he worked towards his own orgasm. “I’m going to pump you full of another load and plug it back up with that dildo so when we go downstairs you’re even more full of me without your family knowing.”

He didn’t mention that fucking Dean’s sweet, innocent little brother was also  _very_  high on his list. There was little doubt in his mind that he could coax Sam into letting Castiel fuck him until his little hole was sloppy with it.

Castiel came inside Dean and pressed Dean’s body into the carpet before finally pulling out. He found Dean’s dildo and pushed it back inside before pressing a kiss on the end of it.

“I love having you fucked and stuffed full.” the words were rough. He wasted no time jerking Dean around so he could press him into the carpet on his back.

Castiel sucked a mark onto the skin above Dean’s collarbone before leaning up to press his lips to Dean’s. They stayed like that, Castiel pinning Dean’s lax body into the carpet, before finally separating to clean up before going back downstairs.


	3. Chapter 3

 

Sam blinked when he heard a muffled sound. His eyes darted around and not seeing anyone he started towards the noise with curiosity. It sounded a bit like someone might be in pain, the sound reminded him a bit of a low kind of moan, as he got closer and closer to the source. The sound was louder, accompanied by someone speaking, as Sam walked towards a prayer room where the door was ajar.

He moved quietly and slowly pushed the door open to see his brother on his knees, legs spread wide for support, with his ass in the air. Dean was completely naked and his brother’s friend was also on the floor with him in the same exact state.

From his angle Sam could see that Castiel had three fingers buried deep in Dean’s ass, lazily pumping in and out, as moans and broken sobs escaped into the room from his older brother’s mouth. “ _Please_.” it was rough and Sam could see Dean’s throat working as Castiel continued his slow, teasing pace. “Fuck me.”

The words had Sam jerking in shock and leaning forward to see better. He had always looked up to his older brother and he wanted to understand what Dean was doing.

His brother’s plea had the fingers in Dean’s hole pausing and Sam watched as they slowly pulled out. Sam’s mouth hung open and the air in his lungs seemed frozen as he watched Castiel shift his brother around so he could tie Dean’s hands with a rosary.

The entire thing was clearly not meant for other eyes but Sam couldn’t tear his eyes way as the older guy guided a large cock inside his brother’s ass. It was thick and long. He didn’t think he could possibly fit where it appeared that Castiel was going to put it but that didn’t seem to bother Castiel. Sam thought of his own cock, small and soft, as he stared at Castiel’s in horrified fascination.

Sam could see Castiel’s cock disappearing, inch by inch, as Dean’s mouth worked and a needy sob escaped once more. “What would people say if they knew such a nice boy was a complete whore? That Dean Winchester was taking a dick inside a church?”

Castiel’s voice was husky and Sam shifted on his feet as his fingers gripped at the door.

The cock pressing forward into Dean disappeared when Castiel’s hips were flush against Dean’s ass and then the sound of a slap against Dean’s thigh startled Sam. He jerked back but didn’t stop staring.

The smack only earned a pitiful moan from Dean and then Castiel was drawing back before thrusting forward. Sam could see where Castiel’s fingers had dug into the flesh of Dean’s hip. A smattering of bruises was obvious when he looked closer.

As Sam watched the rhythm of Castiel thrusting forward seemed to pull more sound from Dean and the sound of balls, so much bigger than Dean’s or his own, slapping against Dean’s ass mixed with the smacking of skin against skin as Castiel fucked Dean into the floor.

Dean’s body moved with each thrust, cheek pressed to the floor, as Castiel placed a hand where Dean’s wrists were bound. He used it as leverage as he moved and Sam felt his body responding.

The unexpected sensation in his gut had confusion filling Sam at the uncomfortable press of his small cock against his dress pants but he couldn’t tear his eyes away from the sight of a man fucking his older brother.

The whole thing was forbidden, a sin, but Dean seemed so lost in it and if Dean was doing it then it must not be that wrong. Strangled moans and desperate cries for harder, for more, reached Sam’s ears. Sure if Dean could do it then it wasn’t wrong. Maybe he’d misunderstood?

“Love fucking you.” Castiel breathed out as his fingers flexed against Dean, “This is just what you needed.” his hips were still snapping forward, hitting against Dean’s ass as he made sure to fuck deep each time. “You wanted your ass pounded in a prayer room of all places. Moaning like a whore and begging for more.” Castiel’s cheeks were flushed with arousal, “You love feeling my dick sliding in and out of your hole, don’t you?”

Dean’s eyes slid closed and his mouth dropped open, Sam could see his brother couldn’t form words anymore. Sam felt hot and uncomfortable but he couldn’t look away.

“Not even going to plug you after. I want my come leaking out of you, running down your legs while we’re here.” Castiel snarled as his thrusts became wilder and the sound of them fucking was even louder, “Then when we get back to my place we’re going to get high and you’re going to show me how much you love riding my dick.”

Dean’s mouth went slack as his cock jerked and he came untouched while Castiel kept thrusting forward. As his orgasm washed over him his ass clenched tightly around Castiel while Castiel kept fucking forward until he slammed deep, hips jerking, as he came with a groan.

Sam jerked back from the doorway, cheeks flushed and mouth dropped open, before he glanced down at the hard-on in his pants. Confusion filled him and he stumbled away from the prayer room on shaky legs as he tried to figure out what just happened no noticing the wicked blue eyes watching him with hungry greed.

 


	4. Chapter 4

 

Castiel had been delightfully right.

Sam had come onto campus to visit Dean, his parents all too happy to leave him with Castiel who said he was on his way to Dean’s, and Castiel wasn’t one to pass up that kind of opportunity. Sam had spent the time flushed, unable to meet his eyes and mumbling whenever Castiel spoke to him.

They had a few hours until Dean got out of class and Castiel looked at the pretty teenager twitching in obvious embarrassment. He didn’t bother hesitating before hauling Sam forward and manhandling him so he was straddling Castiel with wide, shocked eyes.

His hand moved down to grip Sam’s ass and pulled him until their clothed cocks were up against each other.

“Wha…what? Cas?” Sam’s face was red and Castiel smirked. His high from earlier was fading but he had a pretty little distraction right there in front of him. “This is…you can—”

Castiel gripped him and moved his hand to press a finger against Sam’s mouth. “Shhhhh, Sam.” He breathed out with amused delight, “It’s ok. Dean said it was.”

Sam stared at him and then, hesitantly, he blinked. “He did?” his voice was small and unsure. It probably came from such a strict household and a desperate wish to make his brother proud.

“Of course.” Castiel nodded, “He told me how good you were and how, he knew, that you would be just as good for me as he is.” He knew exactly where to push, “Did he lie to me, Sam?”

“No!” Sam immediately jerked his head, “Dean would  _never_  lie! I can be just as good as Dean can be.”

“Oh? So you’re going to be good for me?” he asked with a low, teasing voice. “Are you going to be a good boy for me like Dean was in the prayer room? Where you were watching us?”

Sam was staring at him with wide eyes and Castiel kept his expression curious, mild, as he waited.

“Sam?”

“Yes.” He shivered, “I’ll be good. If Dean said I could be then I will.”

“You want to impress your big brother, don’t you? Want me to tell him you were good for me?”

Sam shuddered and Castiel’s hands kneaded Sam’s ass.

It wasn’t plump like Dean’s but there wasn’t a question that the young Winchester’s ass would be very tight and it felt good filling his hands. Castiel was rock hard and aching to bury himself inside a tight, virgin hole so he could fuck until he’d ruined it.

“I do.” Sam bit his lip, “I can be good. I promise.”

Castiel grinned and pulled him down to press a kiss against Sam’s lips. “I know you can. Dean told me so.” He flicked his eyes around the room. “Since you’re a good boy I want you to take off all your clothes, place them on the chair right there and get on the bed in the same position you saw Dean in.”

Sam’s legs were shaking when he stood and Castiel watched him clumsily strip before climbing on the bed. It wasn’t the perfect position but Castiel could fix that. He stood up, groaning lowly at the ache in his cock, as he crossed the room to Sam.

He was sure the teenager would grow more into his body when he got older but there was something about dirtying up another boy raised just like Dean and something even better about taking his virginity.

Castiel spread Sam’s legs wider until the teenager whimpered at the stretch and pushed his hand against Sam’s back until his body was bowed beautifully. “Hands behind your back.” He tied them there with Dean’s belt and turned his attention to the pink, untouched hole on offer.

He was going to wreck that little hole.

Castiel went to the wardrobe, pulled out one of Dean’s thicker plugs, a ball-gag, a pointed cap and a large bottle of lube from the box stored in there. They were all items he’d placed in there on previous trips. He took off the cap and twisted on the pointed end that he’d gotten for this exact reason.

The end pushed against Sam’s hole and he shoved it in earning a gasp. Sam jerked and Castiel gripped him.

“No moving. I thought you said you could be good.”

Sam nodded jerkily and stilled again.

“There we go.”

He pushed the end in further and squeezed a healthy amount of lube directly into Sam’s ass. It would make things a bit easier with stretching and preparation. Plus he loved a sloppy fuck and coupled with Sam’s virgin tightness it would be a Hell of a fuck.

Castiel set the bottle down after slicking his fingers and turned to Sam’s ass. The first finger had Sam crying out and tensing. “Do you need help being quiet? It’s ok if you do. Sometimes Dean needs help to be good.”

Sam turned and stared at him with pained eyes but Castiel could see how determined he was to be as good as Dean.

“I need help.”

“Good boy.”

Castiel pulled back, grabbed the ball-gag and hauled Sam up to shove it into his mouth after telling him to open. It stretched Sam’s mouth wide open, the ball filling his mouth, before it was secured in place. The straps bit into the skin of Sam’s cheeks and Castiel lowered him back down, shoving him back into a proper position, before resuming his task.

There were muffled cries, whimpers and gasps as he slowly and methodically fingered Sam’s ass until it was loose enough he didn’t have to worry about tearing.

He added more lube inside Sam’s ass and squirted some to rub on Sam’s now red rim. It had the teenager jerking and twitching at the sensation but Castiel merely stroked his trembling thigh.

“You’re doing so well. Are you ready? Are you ready to show me that you can be just as good as Dean? Just as good as your older brother said you could be? Can you take every inch of my dick like Dean can?”

Sam nodded, desperate and wide-eyed, as Castiel freed his cock. He climbed further onto the bed, situated his knees so they were resting at the inside of Sam’s on the mattress to keep Sam positioned as he wanted, before he guided his cock forward.

It looked even bigger so close to Sam’s ass and loosened hole. Anticipation flooded his body. He’d fucked teenagers prettier than Sam but there was something more about this one considering the Winchester family. He knew how hard it had been to get Dean and that it would have been impossible for Sam if the youngest Winchester hadn’t seen Dean getting fucked.

Castiel pushed the fat head of his cock against Sam and started working it inside. The sounds Sam was releasing made him grateful he’d thought to gag the teenager because there wasn’t a question that someone would have heard.

“So good. So fucking  _tight_.” He gritted his teeth as inch after inch spread Sam’s ass wide open. Castiel watched avidly as his cock stretched Sam’s hole and started to disappear. It took a while but finally,  _finally_ , his balls were pressed up against Sam’s ass and glorious tight heat viciously clenched down on him.

He could blow his load right now at how fucking good it felt.

Castiel curled his hand around Sam’s bound wrists and his other hand dug into Sam’s hip as he pulled back. Slowly he moved back until just the head of his cock was caught inside before he slammed back in with a grunt.

Sam wailed into his gag and shuddered, body tightening impossibly down on him, as Castiel’s cheeks flushed and his lips parted.

“That’s it.” He breathed out, “Just like your brother, aren’t you?”

Castiel lost himself to the enjoyable sensation of fucking. He pounded himself in and out of Sam’s ass, balls slapping loudly against Sam, as the cheap mattress under them creaked and the headboard knocked on the hall.

At least people on Dean’s floor were used to fucking happening in Dean’s room and right now most of them were in class.

Castiel moaned as his hips snapped forward quicker and quicker, Sam jerking underneath him and moaning brokenly into his gag, as Castiel chased his orgasm and relished crossing another thing off his list.

He’d known the instant he’d seen Sam’s wide innocent eyes that he had to have a taste of him just like he’d done with Dean. If luck favored him then he’d have plenty more opportunities to dirty up both Winchesters. It was far too addictive to see all the different things he could talk Dean into now and he wondered how many he could talk Sam into under the guise that Dean had told him Sam could be good too.

It might even be possible to train Sam into being an even better, needier slut for his cock.

His pace picked up until he was slamming into Sam and choked moans reached his ears as he worked himself in and out of Sam’s body. Castiel’s orgasm twisted and built inside of him, coiling and hot, until he slammed himself balls deep and came with a groan of enjoyment.

Castiel fucked himself into Sam in short thrusts as he chased the pleasure of his orgasm in the tight clench of Sam’s ass.

“Dean was right.” He breathed in a wrecked voice, “You can be good just like him.”

His soft cock slipped free of Sam’s ruined ass, the hole now dark red and puffy, while his eyes feasted on the sight of lube and his come dribbling out of Sam’s gaping hole caught his full attention.

Castiel lubed up the large plug, pushed the mess back inside of Sam’s ass and worked the thick plug past the resisting ring of Sam’s hole. It had a muffled cry escaping Sam but soon enough Sam’s hole gave and the thick ball of the plug sunk in to keep his release nestled deep inside Sam.

He wiped the rest of the mess up with one of Dean’s dirty shirts and rolled Sam over onto his back. The bound, gagged and fucked teenager stared at him with glassy eyes, flushed cheeks and a soft little cock.

“Rest.” He grinned in satisfaction. “I’ll wake you up in an hour or so.”

Castiel stretched. There was nothing like getting high after a delicious fuck. He lit up and breathed in, closer to Sam and blowing smoke in the teenager’s face. By the time he was finished with his second one Sam was clearly high himself where he lay on the bed painting such a pretty picture.

**Author's Note:**

> This was a very different version of the Winchesters and Castiel. I'm not making a commentary on anything but merely writing to fill the prompts this story was created to fill.
> 
> Not sure if this was anyone's thing or if anyone other than the prompter(s) will enjoy it. I'll see by your comments, won't I? This one was missing the last four paragraphs and a quick edit before I could post it.
> 
>  
> 
> \--Yes I'm using this next bit on each of the new fics I post from my folder since it fits all of them (yay copy and paste).--
> 
> Again I'm still going through that folder on my laptop though I keep getting a bit distracted so this is getting dragged out a bit. This fic is another one that was waiting to be finished, fixed and posted.
> 
> Leave a comment and let me know what you thought! Your comments and thoughts are always appreciated!


End file.
